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How to get fromChicago to Westchester Countyby plane, train, train (Amtrak), bus, car, shuttle, or bus (Flixbus)

Find Transport to Westchester County

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There are 10 ways to get from Chicago to Westchester County by plane, train, train (Amtrak), bus, car, shuttle, or bus (Flixbus)

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Fly Chicago Midway International Airport to Laguardia Airport, train

    best
    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the train from 125th Street - Harlem to Chappaquatrain train
    5h 24m
    $226–680

  2. Fly Chicago O'Hare International Airport to Westchester County Airport, train

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    2. Take the train from White Plains to Chappaquatrain train
    6h 19m
    $72–349

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Croton-Harmon Amtrak Stationtrain train Lake Shore Limited
    20h 50m
    $519–796

  4. Bus, train

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore Downtown Bus Station to Port Authority Bus Terminalbus bus
    3. Take the train from Grand Central Terminal to Chappaquatrain train
    23h 6m
    $195–299

  5. Drive  813.2 mi

    1. Drive from Chicago to Westchester Countycar car 813.2 mi
    13h 45m
    $139–201

  6. Fly Chicago O'Hare International Airport to Laguardia Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane plane ORD - LGA
    2. Take the train from 125th Street - Harlem to Chappaquatrain train
    5h 43m
    $136–500

  7. Fly Chicago O'Hare International Airport to John F. Kennedy International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to John F. Kennedy International Airport (JFK)plane plane ORD - JFK
    2. Take the train from Grand Central Terminal to Chappaquatrain train
    5h 54m
    $378–891

  8. Fly Chicago O'Hare International Airport to Newark Liberty International Airport, shuttle, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Newark Liberty International Airport (EWR)plane plane ORD - EWR
    2. Take a shuttle bus from Newark Airport Terminal B to Grand Centralshuttle bus
    3. Take the train from Grand Central Terminal to Chappaquatrain train
    6h 30m
    $168–723

  9. Fly Chicago Midway International Airport to Philadelphia International Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Philadelphia International Airport (PHL)plane plane MDW - PHL
    2. Take the train from 30th Street Station to Ny Moynihan Train Hall At Penn Stationtrain train
    3. Take the train from Grand Central Terminal to Chappaquatrain train
    7h 15m
    $188–930

  10. Bus (Flixbus)

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2640 / ...
    23h 30m
    $166–242

Chicago to Westchester County by train and bus (Amtrak)

Calendar7Weekly Services
Duration20h 50mAverage Duration
Ticket$519Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Westchester County.ExpandLaunch map view
  • Distance: 769 mi
  • Duration: 5h 24m

What companies run services between Chicago, IL, USA and Westchester County, NY, USA?

Amtrak operates a train from Chicago Union Station to Croton-Harmon Amtrak Station once daily. Tickets cost $500–800 and the journey takes 19h 23m. Alternatively, Flixbus USA operates a bus from Chicago Bus Station to New York Midtown 4 times a day. Tickets cost $150–240 and the journey takes 20h 10m.

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